Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00259)
Name
Etravirine
Synonyms    Click to Show/Hide the Synonyms of This API
Etravirine; 269055-15-4; Intelence; Etravirine (TMC125); TMC-125; TMC125; TMC 125; R-165335; UNII-0C50HW4FO1; 4-((6-Amino-5-bromo-2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile; 4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE; R165335; C20H15BrN6O; 0C50HW4FO1; CHEMBL308954; CHEBI:63589; 4-[[6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]-4-PYRIMIDINYL]OXY]-3,5-DIMETHYLBENZONITRILE; Benzonitrile, 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-; 4-(6-Amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile; Intelence(TM); DAPY deriv; 4-(6-amino-5-bromo-2-(4-cyanophenylamino)pyrimidin-4-yloxy)-3,5-dimethylbenzonitrile; Benzonitrile, 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-; Benzonitrile,4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl-; Intelence (TN); 1142095-93-9; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenoxy)pyrimidin-2-yl]amino]-2,3,5,6-tetradeuteriobenzonitrile; Diaminopyrimidine deriv; etravirine;; Etravirine (JAN/USAN/INN); Etravirine-d8; Etravirine [USAN:INN:BAN:JAN]; R 165335; Etravine; Etravirine; 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile; R165335-TMC125; PubChem22565; TMC-125/R-165335; 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile; SCHEMBL52691; DTXSID30181412; HMS3651P20; ZINC602632; BCP03562; EBD13985; EX-A4282; TMC 125;; TMC-125;; ABP001081; BDBM50103642; MFCD09837879; 4-({6-amino-5-bromo-2-[(4-; AKOS015896355; AC-8503; BCP9000006; CCG-269074; CM14420; CS-0435; DB06414; HE-0088; PB32778; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile; 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethyl-benzonitrile; NCGC00345885-04; AK172046; BC004800; HY-90005; BCP0726000193; AB0030712; DB-067700; AM20080899; cyanophenyl)amino]pyrimidin-4-yl}oxy)-3,5-; FT-0658058; FT-0668442; FT-0668443; SW219570-1; B-1795; D04112; AB01566873_01; A818671; Q414762; SR-01000944895; J-513179; R165335;; R165355;; SR-01000944895-1; 4-(6-amino-5-bromo-2-(4-cyanophenylamino)pyrimidin-4-ylamino)-3,5-dimethylbenzonitrile; 4-[[4-amino 5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]benzonitrile; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]-amino]benzonitrile; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]-benzonitrile; 4-[[4-amino-5-bromo-6-(4-cyano-2,6-dimethylphenyloxy)-2-pyrimidinyl]amino]-benzonitrile;; 4-[[6-amino-5-bromo-2-(4-cyanoanilino)-4-pyrimidinyl]oxy]-3,5-dimethylbenzonitrile; 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3,5-dimethyl benzonitrile; 4-[6-amino-5-bromo-2-(4-cyano-phenylamino)-pyrimidin-4-yloxy]-3,5-dimethyl-benzonitrile; 4-((6-amino-5-bromo-2-((4-cyanophenyl) amino) pyrimidin-4-yl) oxy)-3, 5-dimethylbenzonitrile; 4-[[6-amino-5-bromo-2-[(4-cyanophenyl)amino]-4-pyrimidinyl]oxy]-3, 5 Cdimethylbenzonitrile; 4-[6-azanyl-5-bromanyl-2-[(4-cyanophenyl)amino]pyrimidin-4-yl]oxy-3,5-dimethyl-benzenecarbonitrile
Clinical Status
Approved
Disease Indication Human immunodeficiency virus infection ICD-11: 1C60 [1]
PubChem CID
193962
Formula
C20H15BrN6O
Canonical SMILES
CC1=CC(=CC(=C1OC2=NC(=NC(=C2Br)N)NC3=CC=C(C=C3)C#N)C)C#N
InChI
1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
InChIKey
PYGWGZALEOIKDF-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=193962"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 435.3 Topological Polar Surface Area 121
XlogP 4.5 Complexity 609
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Etravirine 100 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Hypromellose; Silicon dioxide; Cellulose, microcrystalline
                   Dosage Form Oral Tablet
                   Company State of Florida DOH Central Pharmacy
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Etravirine 200 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Croscarmellose sodium; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions; Janssen Products; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
References
1 FDA label for approved etravirine from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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